dimethyl 2-cyano-1,6-dihydro-6-oxo-1-phenyl-3,4-pyridinedicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 2-cyano-1,6-dihydro-6-oxo-1-phenyl-3,4-pyridinedicarboxylate
• 英文别名: Dimethyl 2-cyano-6-oxo-1-phenylpyridine-3,4-dicarboxylate
• 化学式: C₁₆H₁₂N₂O₅
• 分子量: 312.282
• InChiKey: SIFDXLFOKRMWJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  96.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  马来酸二甲酯 、 5-chloro-3-(diethylamino)-1-phenyl-2(1H)-pyrazinone 以 甲苯 为溶剂， 反应 72.0h， 以88%的产率得到dimethyl 2-cyano-1,6-dihydro-6-oxo-1-phenyl-3,4-pyridinedicarboxylate
  参考文献：
  名称：

  Cycloaddition of 3-Amino-5-chloro-2(1H)-pyrazinones and Olefins:  Ring Transformation into 3-Amino- or 6-Cyano-Substituted 2-Pyridinone Systems

  摘要：

  The cycloadducts formed from the Diels-Alder reaction of 3-amino-5-chloro-2(1H)-pyrazinones with methyl acrylate in toluene are subject to two alternative modes of ring transformation yielding either methyl 6-cyano-1,2-dihydro-2-oxo-4-pyridinecarboxylates, e.g. 12a,b (loss of amine substituent), or the corresponding 3-amino-6-cyano-1,2,5,6-tetrahydro-2-oxo-4-pyridecarboxylates, e.g. 15a,b. From the latter compounds, 3-amino-2-pyridinones can be generated through subsequent loss of HCN. A mechanism accounting for the loss or retention of the amine substituent is based on (1) the effects observed for each reaction mode when varying the substituents in both reaction partners and (2) the exclusive retention of the amine substituent when replacing toluene with the basic solvent pyridine.

  DOI：

  10.1021/jo951016o

文献信息

• Cycloaddition of 3-Amino-5-chloro-2(1<i>H</i>)-pyrazinones and Olefins:  Ring Transformation into 3-Amino- or 6-Cyano-Substituted 2-Pyridinone Systems
  作者：Stef M. Vandenberghe、Kris J. Buysens、Lieven Meerpoel、Patrick K. Loosen、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1021/jo951016o

  日期：1996.1.1

  The cycloadducts formed from the Diels-Alder reaction of 3-amino-5-chloro-2(1H)-pyrazinones with methyl acrylate in toluene are subject to two alternative modes of ring transformation yielding either methyl 6-cyano-1,2-dihydro-2-oxo-4-pyridinecarboxylates, e.g. 12a,b (loss of amine substituent), or the corresponding 3-amino-6-cyano-1,2,5,6-tetrahydro-2-oxo-4-pyridecarboxylates, e.g. 15a,b. From the latter compounds, 3-amino-2-pyridinones can be generated through subsequent loss of HCN. A mechanism accounting for the loss or retention of the amine substituent is based on (1) the effects observed for each reaction mode when varying the substituents in both reaction partners and (2) the exclusive retention of the amine substituent when replacing toluene with the basic solvent pyridine.